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DOI: 10.1039/A700549K (Paper) Reference Section for: Chem. Commun., 1997, 1059-1060

Use of the p-nitrobenzyloxycarbonyl group as an orthogonal amine protecting group in the synthesis of β-GlcNAc terminating glycosides

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Xiangping Qian and Ole Hindsgaul

Abstract

The p-nitrobenzyloxycarbonyl group serves as a participating group in the stereoselective formation of 2-amino-β-glucosides and as an N-protecting group which can be readily removed either by hydrogenolysis or by reaction with sodium dithionite under neutral conditions.

References

  1. A. Varki, Glycobiology, 1993, 3, 97 Search PubMed; R. A. Dwek, Chem. Rev., 1996, 96, 683 CrossRef CAS.
  2. J. Banoub, P. Boullanger and D. Lafont, Chem. Rev., 1992, 92, 1167 CrossRef CAS; S. H. Kahn and O. Hindsgaul, in Molecular Glycobiology, ed. M. Fukuda and O. Hindsgaul, IRL, Oxford, 1994, ch. 5 Search PubMed.
  3. F. Barresi and O. Hindsgaul, J. Carbohydr. Chem., 1995, 14, 1043 CAS; T. B. Grindley, in Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O'Neill, Harwood Academic, Amsterdam, 1995, p. 241 Search PubMed.
  4. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, NY, 1991, p. 339 Search PubMed.
  5. L. Zervas and S. Konstas, Chem. Ber., 1960, 93, 435 CAS.
  6. K. Heyns, R. Harrison and H. Paulsen, Chem. Ber., 1967, 100, 271 CAS; J. Lessard, H. Driguez and J. P. Vermes, Tetrahedron Lett., 1970, 4887 CrossRef CAS.
  7. M. Imoto, H. Yoshimura, T. Shimamoto, N. Sakaguchi, S. Kusumoto and T. Shiba, Bull. Chem. Soc. Jpn., 1987, 60, 2205 CAS; V. Pozsgay, in Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry, ed. H. Ogura, A. Hasagawa and T. Suami, Kodansha, Tokyo, 1992, p. 199 Search PubMed.
  8. P. Boullanger, M. Jouineau, B. Bouammali, D. Lafont and G. Descotes, Carbohydr. Res., 1990, 202, 151 CrossRef CAS.
  9. D. Lafont, P. Boullanger, J. Banoub and G. Descotes, Can. J. Chem., 1990, 68, 828 CAS; D. Lafont, P. Boullanger and B. Fenet, J. Carbohydr. Chem., 1994, 13, 565 CAS.
  10. R. R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 1994, 50, 21 Search PubMed.
  11. F. A. W. Koeman, J. W. G. Meissner, H. R. P. van Ritter, J. P. Kamerling and J. F. G. Vliegenthart, J. Carbohydr. Chem., 1994, 13, 1 CAS; P. Stangier and O. Hindsgaul, Synlett, 1996, 179 CrossRef CAS.
  12. (a) J. S. Debenham, R. Madsen, C. Roberts and B. Fraser-Reid, J. Am. Chem. Soc., 1995, 117, 3302 CrossRef CAS; (b) J. S. Debenham and B. Fraser-Reid, J. Org. Chem., 1996, 61, 432 CrossRef CAS.
  13. J. C. Castro-Palomino and R. R. Schmidt, Tetrahedron Lett., 1995, 36, 5343 CrossRef CAS.
  14. F. D. Bellamy and K. Ou, Tetrahedron Lett., 1984, 25, 839 CrossRef CAS.
  15. E. Guibe-Jampel and M. Wakselman, Synth. Commun., 1982, 12, 219 CAS.
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